The Self-Employed Tax Trap – Why Independent Contractors Get in Trouble

Episode Summary

In this episode of Resilience and Resolve, tax attorney Lance Drury uncovers why so many self-employed individuals and independent professionals fall into the IRS trap. From missed quarterly estimated tax payments to poorly documented expenses, Lance explains the most common mistakes freelancers and business owners make—and how to avoid snowballing tax problems.

He shares practical strategies for staying compliant, tips for managing unpredictable income, and why separating personal and business finances is crucial. Lance also reveals real-life client stories, including a business that faced million-dollar levies and how his team resolved it.

Whether you’re a freelancer, gig worker, or small business owner, this episode is packed with actionable advice to help you stay out of IRS trouble.

Key Timestamps

00:21 – Why self-employed individuals often fall behind on taxes
01:13 – The hidden financial struggles of freelancers and gig workers
02:23 – Common mistakes in estimating tax liability
03:33 – How failing to track expenses can lead to a bigger tax bill
04:18 – Why monthly payments prevent spending money meant for taxes
06:29 – The difference between 1099 and W-2 income in IRS compliance
07:41 – A real-life case of million-dollar levies and how they were resolved
09:36 – How to avoid “pyramiding” payroll tax liabilities
10:49 – The critical first step if you’re already behind on taxes
11:25 – Why revenue officers create urgency in payroll tax cases

About the Show:

“Resilience and Resolve with Lance Drury” provides practical legal insights into IRS matters, tax law, and financial defense strategies. Each episode explores timely and complex tax issues with real-world examples and expert analysis from Lance Drury and his experienced legal team.

Follow Lance Drury for more tax resolution insights:
🌐 LanceDruryLaw.com